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The Rom-Com Sidekick Awards

Because as Judy Greer will surely tell you: No romance exists in a vacuum

Sony/Paramount/Ringer illustration

When you find the theme week you want to spend the rest of your life with, you want the rest of your life to start as soon as possible. Thankfully, The Ringer hereby dubs this week Rom-Com Week, a celebration of one of the most delightful, captivating genres in film. Head to the top of the Empire State Building, order what she’s having, and join us as we dig into everything the rom-com has had to offer over the years.


No romance exists in a vacuum, and surrounding every crush is a village with a vast infrastructure. Coworkers workshop text messages. Nosy moms mean well but undermine, too. Best friends provide harsh truths, terrible advice, and various intoxicants. Exes loom, and bosses just don’t understand! It is all a bustling emotional Busytown, filled with flowermongers and high school reunions and chase scenes involving taxi cabs.

Which is why the best romantic comedies don’t focus only on the central pairs (or trios!) as they dance their will-they-or-won’t-they two-step. The best romantic comedies delight in asking “who are they?” about all the peripheral people populating the outskirts of the dance floor, too.

From neighborhood clerks to national athletes, from affable dads to basket-case gal pals, all these supporting rom-com characters are there to keep the plot moving, keep the protagonists focused (or distracted), keep the vibes light, and keep the lies straight. Whether they are the type to cry at weddings or speak up and never hold their peace, here are some of the most memorable family members, friends, and frenemies in the rom-com universe …

Most Elite Operational Collaborator: Cyn (Joan Cusack) in Working Girl

Influence on the main characters: It may turn out to be a relic of a bygone era, but there are few relationships more pure, and more logistically vital, than the workplace best friend. The gossip! The coffee breaks! The after-work happy hour! The complicity in fooling a handsome businessman about one’s identity in an effort to transcend one’s pigeonholed existence! As a willing and wise-cracking accomplice to Melanie Griffith’s Tess McGill in Working Girl, the eyeshadowed and accented Cyn (Cusack) puts on a performance that is as big and bold as her bangs, stealing the show and helping Tess get the job and the guy in the process.

Influences on our culture: If you squint, “Coffee, tea, or me?” is in some ways an ancient ancestor of Chuckie’s over-enunciated “retainer.” (Also: “Ya decent?”—one of those things you don’t hear so much anymore!)

Others of note: As the longtime drinking buddy of (and aspiring mini-golf investor alongside) Kurt Russell’s Dean Proffitt in Overboard, Billy Pratt (That Guy Mike Hagerty) helps his pal pull off a scheme that is rather messed up, even by the lax ethical standards of rom-com premises: Tricking an amnesiac rich lady (Goldie Hawn) into believing that she’s Dean’s beleaguered wife. To that end, Billy’s ops include doctoring photographs and convincing “Annie” that he’s the one responsible for a pair of mysterious panties. Highly moral? No. A guy you’d call in a bind? Absolutely.

Most Chaotic Double Date Hang: Jess and Marie (Bruno Kirby and Carrie Fisher) in When Harry Met Sally

Influence on the main characters: After years of flirtatious but cantankerous interactions, Harry and Sally (Billy Crystal and Meg Ryan) decide to try setting one another up with their respective best friends, Jess and Marie. But the two plus-ones smartly cut out their forever-equivocating middlemen pals and fall directly for each other instead. And over the couple of years that ensue, they become an illuminating domestic juxtaposition, for better and worse, to their more stubborn, wayward, phone-hogging main-character counterparts in the film.

Influences on our culture: Every time I bicker with my spouse I think about wagon-wheel coffee tables!!!

Others of note: Debbie and Pete (Leslie Mann and Paul Rudd) in Knocked Up are part cautionary tale and part aspirational partnership too. She is controlling and insecure; he sneaks out of the house to carry on an emotional affair with fantasy baseball. And yet with the help of Alison and Ben (Katherine Heigl and Seth Rogen) they also realize that they really do love and cherish each other. It just takes some club bouncer rejection and shrooms in Vegas to arrive at that conclusion. Who among us can’t relate to that?

Best Advice-Dispensing Athlete: Rod Tidwell (Cuba Gooding Jr.) in Jerry Maguire

Influence on the main characters: “Single mothers don’t date,” Rod Tidwell, the son of a single mother, explains to Jerry Maguire in one of the film’s most real-talk scenes. “They’ve been to the circus, you know what I mean? They’ve been to the puppet shows, and they’ve seen the strings.”

Influences on our culture: It’s because of Tidwell’s character that viewers were blessed with the bounty of Tom Cruise insisting: “I didn’t. Shoplift. The pootie!”

Others of note: LeBron James as LeBron James in Trainwreck. Cleveland is great for the whole family, you know? And speaking of GOAT athlete performances …

First-Ballot Unanimous All-Shart Team Captain MVP Hall-of-Rainer: Sandy Lyle (Philip Seymour Hoffman) in Along Came Polly

Influence on the main characters: Along Came Polly may be a bit of a dud as a movie overall, but it features two of the funnier auxiliary parts in the history of the genre: Hank Azaria’s randy scuba instructor Claude, and Sandy Lyle, the sweaty, congested, former-child-actor BFF to Ben Stiller’s jilted main character Reuben. Sandy Lyle is a towering performance by Seymour Hoffman, huffing with cocky, wrong wisdom whether he’s advising Reuben on his relationship troubles, taking over for him in the boardroom with throat-clearing abandon, or scattering raindrops on the pickup basketball court. There is no one quite like this guy, and yet he reminds every viewer of this one guy they know.

Influences on our culture: Immeasurable, just like his wingspan and his libido. Sandy Lyle is a man who selflessly elevated shart awareness and the jogger-cut sweatpant revival into the mainstream. He ensured it would be physically impossible for an entire generation to touch a basketball without immediately screaming “Raindrop!” or “Iceman!” or “White Chocolate!” before launching a mighty brick. We stan this big horny goat, the best rom-com shart king that ever was. Let it rain!

Others of note: If you crossed Spike (the shaggy, Pandora’s box–seeking, underwear-lounging roommate in Notting Hill) with Freddie Bauer (the racquetball-playing, penis-in-Swedish-pronouncing, Penthouse-reading sidekick in Splash) you’d have a character approximating the skill kit of Sandy Lyle, a true five-tool generational talent.

Most Emotionally Fraught Baked Thing: The Fruitcake in The Apartment

Influence on the main characters: In the 1960 movie The Apartment, Jack Lemmon’s just-plugging-along character C.C. Baxter explains to Shirley MacLaine’s Fran Kubelik what became of the ex-girlfriend who long ago broke his heart. Every Christmas, he says, she sends him a courtesy fruitcake—that famously sticky confection served with cherries and pity. By the end of the movie, however, a follow-up reference to the fruitcake gives it new resonance: no longer is it just a symbol of a lonely past, it’s now a nod toward a shared joke, and maybe even a shared future?

Influences on our culture: “There is only one fruitcake in the world,” Johnny Carson posited on the Tonight Show in 1985, “and people keep passing it on when they get one.” While there’s no indication that The Apartment had anything to do with this joke, there’s also no indication that it didn’t.

Others of note: A real cornucopia of carb-heavy delights, from the misunderstood Bundt in My Big Fat Greek Wedding—my kingdom for a meme mashing up this scene with Oprah saying “were you silent … or were you silenceD?”—to the freshly baked Italian loaves accentuating Nicolas Cage’s bonkers opening flourishes in Moonstruck.

Most Emotionally Distraught Fake Shrink: Michelle (Kathryn Hahn) in How to Lose a Guy in 10 Days

Influence on the main characters: Michelle represents many tentpole archetypes in this film, but what distinguishes her is the way she encompasses them all at once: a coworker at a women’s magazine (called Composure) who is both a weepy, cautionary basket case and a cool, collected operative sneaking dishy sex questions into a faux therapy sesh.

Influences on our culture: The gift of Hahn herself. While this role was small, it was a breakout performance, a project she shot right out of grad school. In the years that followed she quickly appeared in movies ranging from Anchorman to A Lot Like Love to The Holiday, and she is, blessedly, everywhere now.

Others of note: n/a; this is a pretty niche one.

Most Formidable Ex: Kevin Rawley (Owen Wilson) in Meet the Parents

Influence on the main characters: “I was really lucky, I was able to salvage that wood from an old seaman’s chapel on Nantucket,” says the cable-knitted Kevin, ex-boyfriend to dear Pamcakes and amiably nasal antagoniste to Ben Stiller’s Greg Focker in Meet the Parents. From the adventurous and progressively outlandish old framed couples photos of himself and Pam to his unceasing hospitality and enlightened acceptance of fellow craftsman Jesus Christ (a.k.a. “JC”), Kevin is a benevolent final boss of a former flame and the perfect foil for the neurotic Nurse Greg.

Influences on our culture: The sun is out, the grill is hot, and the pool is luke!!!

Others of note: In 1979’s Starting Over, Candice Bergen plays the one-upping ex-wife of Burt Reynolds who seems intimidating—she has her masters!—until she starts to sing. Kelly Preston’s Avery Bishop has to be one of the most terrifying on-screen presences ever put to film in Jerry Maguire. And what about the least formidable ex? Well, I’d lament “poor Walter” from Sleepless in Seattle, but then I read this and realized he probably got out just in time.

Most Affable Dad, Dude: Terry (Ray Romano) in The Big Sick

Influence on the main characters: Romano infuses latent humor into a wrenching role, playing a man whose daughter is in a medical coma, whose wife is seething, and who nevertheless just kinda wants to connect with said daughter’s shithead-with-a-heart-of-gold kinda-sorta-former boyfriend. And who can blame him? He is a softy when he’s supposed to be stern, he makes offensive 9/11 remarks when he’s just trying to chat, and he contains multitudes even when he isn’t saying a word.

Influences on our culture: Look, Terry isn’t so much about influencing the culture as he is about respecting the giants of our time, OK? Such as a certain 1994 film directed by Robert Zemeckis. “This is why I don’t want to go online, because it’s never good,” Terry vents as he sits in a hospital waiting room. “You go online, they hated Forrest Gump! Frickin’ best movie ever!” Terry,,,, I agree.

Others of note: Terry’s wife, Beth, played by Holly Hunter, is probably the more traditional rom-com parental figure than her husband, which is to say, the opposite personality. She is highly skeptical and protective, a vibe present in movies ranging from the 1940 film His Girl Friday (poor young Bruce and old Mrs. Baldwin, steamrolled by a bunch of snarky reporters!) to more self-evident fare like Jane Fonda’s Monster-in-Law.

Store Worker Whose “Staff Recs” You Should Check Out, if You Know What’s Good for You: Barry Judd (Jack Black) in High Fidelity

Influence on the main characters: “I knew that Jack would be my secret weapon,” said High Fidelity’s John Cusack in an oral history about the movie, which features both actors as pretentious record store clerks and was something of a breakout part for Black.

Influences on our culture: Barry’s opinions are the stuff of legend, including but not remotely limited to: that “I Just Called to Say I Love You” should ONLY be purchased at the mall; that Jesus and Mary Chain is really great; that it’s perverse to not own Blonde on Blonde; that there is no “The”; and that the new Belle and Sebastian sucks ass.

Others of note: It would absolutely track if it were canon that Steve Zahn’s jaded bookstore worker in You’ve Got Mail is the same guy who’s married to Connie Britton’s galboss in The White Lotus. Like, they met when she was at Barnes & Noble for some succeed-in-business author signing, got bored by platitudes, and overheard him rambling adorably about first-edition Judy Blume. I’d watch that meet-cute any day … preferably on a piece of electronics recommended to me by the fine folks at a place like a neighborhood SmartTech. Like so many of the best supporting characters, after all, they’d have lots of opinions, and they’d always be ready to share them with all the people somewhere out there who are searching, forever, for an answer.

Lifetime Achievement Award for a Captive Audience of Industry: Actress Judy Greer (The Wedding Planner; 13 Going on 30; Wouldn’t You Know It; 27 Dresses; Love Happens; Only One of These Is Made Up)

Influence on the main characters: From a childhood mean girl tormenting Jennifer Garner in 13 Going on 30 to a wedding planner in The Wedding Planner who comes to a Finkel-is-Einhorn-level realization alongside J.Lo, Judy Greer’s rom-com résumé is so expansive that Funny or Die once produced a whole sketch on the subject called “Judy Greer Is the Best Friend”—and that was back in 2014.

Influences on our culture: Also in 2014, Greer wrote a book titled I Don’t Know What You Know Me From: My Life as a Co-Star, which sounds like something that someone in a rom-com would be working on throughout.

Others of note: None. She may be the ultimate supporting character, but the Greer stands alone!